Sodium Methoxide → (5-Chloropyridin-2-yl)methanol
Reaction equation
C[O-].[Na+].C([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=1)(=O)C1C=CC=CC=1>CO>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][OH:12])=[N:15][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium methoxide (1M in MeOH) (0.162 mL, 0.162 mmol) was added to a solution of (5-chloropyridin-2-yl)methyl benzoate Part C (200 mg, 0.808 mmol) in MeOH (47.5 mL) and stirred at RT for 2.0 h. The solvent was removed in vacuo and the crude product was subjected to flash chromatography (silica gel/DCM-MeOH 100:0 to 90:10 gradient) to afford (5-chloropyridin-2-yl)methanol 16D (68 mg, 59% yield) as an off-white solid. LC-MS, [M+H]+=144. 1H NMR (400 MHz, DMSO) δ 8.51 (1H, d, J=2.2 Hz), 7.91 (1H, dd, J=8.4, 2.6 Hz), 7.49 (1H, d, J=8.4 Hz), 5.53 (1H, t, J=5.9 Hz), 4.54 (2H, d, J=6.2 Hz). HPLC-Method 8; 0.76 min.